5-methoxy-3-nitrobenzene-1,2-diamine | 76179-57-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-methoxy-3-nitrobenzene-1,2-diamine
• 英文别名: 5-methoxy-3-nitro-o-phenylenediamine；5-Methoxy-3-nitro-o-phenylendiamin
• CAS: 76179-57-2
• 化学式: C₇H₉N₃O₃
• 分子量: 183.167
• InChiKey: IBMSTSUDOQBTDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-methoxy-3-nitrobenzene-1,2-diamine 在 氢溴酸 、 三乙酰氧基硼氢化钠 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 1-cyclopentyl-4-nitro-1H-benzo[d]imidazol-6-ol hydrobromide
  参考文献：
  名称：

  微波辐射使有机硼酸钾与6-磺酸苯并咪唑的Suzuki-Miyaura交叉偶联

  摘要：

  本文重点介绍了有机三氟硼酸盐作为铃木-宫浦与4-硝基-6-三氟苯并咪唑类化合物在微波辐射下交叉偶联的偶联伴侣的应用。在富电子的1,4-，6-三取代的苯并咪唑核心的6位上形成C–C键具有挑战性，并且无法通过Kumada，Negishi，Stille或Heck偶联策略实现。通过使用三氟硼酸苄基钾作为有机金属偶合伙伴的钯偶合策略可以获得37-70％的产率。

  DOI：

  10.1002/jhet.1109
• 作为产物：
  描述：

  4-甲氧基-2,6-二硝基苯胺 在 ammonium hydroxide 、 硫化氢 作用下， 生成 5-methoxy-3-nitrobenzene-1,2-diamine
  参考文献：
  名称：

  Syntheses in the Quinoxaline Series. Preparation of 7-Methoxy-5-aminoquinoxaline and 7-Methoxy-5-hydroxylaminoquinoxaline

  摘要：

  DOI：

  10.1021/ja01226a009

文献信息

• Pharmaceutical composition containing 3,4-dihydro-3-oxo-2-quinoxalines, novel such quinoxalines and processes for the production thereof
  申请人：ELI LILLY AND COMPANY

  公开号：EP0010426A1

  公开（公告）日：1980-04-30

  A pharmaceutical composition characterized by as active ingredient a 3,4-dihydro-3-oxoquinoxaline of the formula: wherein R and R4 are individually H, NO2 or CH30; R1 and R2 are individually H, NO2, CH3O or halo such that at least one of R, R1, R2 and R4 is otherthan H, such that if neitherR1 and R2 is NO2 orCH3O, both RR1 and R2 are individually halo and both R and R4 are H, and such that one ofR1 and R2 is CH3O only if one of R, R1, R2 and R4 is NO2; R3 is C1-C4 alkyl, C3-C6 cycloalkyl, C3-C4 alkenyl, H or 2-chloroethyl; and n is 0 or 2, e.g. ethyl 6,7-dibromo- 3,4-dihydro-3-oxo-2- quinoxaline carboxylate, and excipients is useful for suppressing viral infection in mammals. All but one of the quinoxalines disclosed are new. The compounds are prepared by reacting an o-phenyiene diamine with an a-ketodibasic acid. Certain of the compounds are prepared by reacting a 6-nitro-4,5- disubstituted aniline with an alkyl malonyl chloride followed by annelation in the presence of sodium ethoxide and then treatment with phosphorus trichloride.

  一种药物组合物，其活性成分为式 3，4-二氢-3-氧代喹喔啉： 其中R和R4分别为H、NO2或CH30；R1和R2分别为H、NO2、CH3O或卤素，这样R、R1、R2和R4中至少有一个不是H，这样如果R1和R2都不是NO2或CH3O，RR1和R2都分别为卤素，R和R4都是H，这样只有当R、R1、R2和R4中的一个是NO2时，R1和R2中的一个才是CH3O；R3 是 C1-C4 烷基、C3-C6 环烷基、C3-C4 烯基、H 或 2-氯乙基；且 n 是 0 或 2，例如例如，6,7-二溴-3,4-二氢-3-氧代-2-喹喔啉羧酸乙酯和辅料可用于抑制哺乳动物的病毒感染。除一种喹喔啉外，所披露的所有喹喔啉都是新化合物。这些化合物是通过邻苯基二胺与 a-酮二元酸反应制备的。某些化合物是通过 6-硝基-4,5-二取代苯胺与烷基丙二酰氯反应，然后在乙醇钠存在下环化，再用三氯化磷处理而制备的。
• Design, synthesis, and testing of an 6-O-linked series of benzimidazole based inhibitors of CDK5/p25
  作者：Prashi Jain、Patrick T. Flaherty、Shuyan Yi、Ishveen Chopra、Gwenyth Bleasdell、Josh Lipay、Yoan Ferandin、Laurent Meijer、Jeffry D. Madura

  DOI：10.1016/j.bmc.2010.11.022

  日期：2011.1

  Alzheimer's disease (AD) is a progressive neurodegenerative disease resulting in cognitive and behavioral impairment. The two classic pathological hallmarks of AD include extraneuronal deposition of amyloid beta (A beta) and intraneuronal formation of neurofibrillary tangles (NFTs). NFTs contain hyperphosphorylated tau. Tau is the major microtubule-associated protein in neurons and stabilizes microtubules (MTs). Cyclin dependent kinase 5 (CDK5), when activated by the regulatory binding protein p25, phosphorylates tau at a number of proline-directed serine/threonine residues, resulting in formation of phosphorylated tau as paired helical filaments (PHFs) then in subsequent deposition of PHFs as NFTs. Beginning with the structure of Roscovitine, a moderately selective CDK5 inhibitor, we sought to conduct structural modifications to increase inhibitory potency of CDK5 and increase selectivity over a similar enzyme, cyclin dependent kinase 2 (CDK2). The design, synthesis, and testing of a series of 1-isopropyl-4-aminobenzyl-6-ether-linked benzimidazoles is presented. (C) 2010 Elsevier Ltd. All rights reserved.
• Some 4,5- and 5,6-Substituted Benzothiazoles
  作者：H. B. Gillespie、Morris Engelman、Samuel Graff

  DOI：10.1021/ja01589a042

  日期：1956.4
• Some New Benzimidazoles and Quinoxalines
  作者：H. B. Gillespie、Morris Engelman、Samuel Graff

  DOI：10.1021/ja01592a027

  日期：1956.6
• Syntheses in the Quinoxaline Series. Preparation of 7-Methoxy-5-aminoquinoxaline and 7-Methoxy-5-hydroxylaminoquinoxaline
  作者：R. H. Mizzoni、Paul E. Spoerri

  DOI：10.1021/ja01226a009

  日期：1945.10